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VPNs
CSH6 Chapter 32
“Virtual Private Networks &
Secure Remote Access”
Justin Opatrny & Carl Ness
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Copyright © 2015 M. E. Kabay. All rights reserved.
Topics
Introduction
Remote-Access VPNs
Site-to-Site VPNs
Extranets
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Copyright © 2015 M. E. Kabay. All rights reserved.
Introduction
Borders Dissolving
Secure Remote Access
Virtual Private Networks
VPN Technology Concepts
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Copyright © 2015 M. E. Kabay. All rights reserved.
Borders Dissolving (1)
 Before Internet access, security → internal
networks
 After ~1993, explosion in Internet connections
 Perimeter firewall reduced access by digital
predators
 How to maintain network security for
employees using mobile technology?
Laptop computers, cell phones
Home, traveling
 How to define extranets for business
partners?
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Borders Dissolving (2)
 Competitive advantage requires
Employee network & information access
From outside workplace
Coping with inclement weather, disruptions
Geographic dispersion of workforce
 B2B requirements growing
Vendors, suppliers, partners
Outsourcing
Support
 B2C demands
Growing expectations from consumers
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Copyright © 2015 M. E. Kabay. All rights reserved.
Secure Remote Access
 Require extensive planning & review
Must not jeopardize safety of
critical information &
information systems
 Primary tools
Virtual Private Networks
(VPNs)
Secured connection
Encrypted tunnel
Extranets
Encrypted connection to
Web application server
outside internal NW
Usually need connections
from server to internal NW for data exchange
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Copyright © 2015 M. E. Kabay. All rights reserved.
Virtual Private Networks
 Basic idea
Create stream of encrypted data through firewall
“Encrypted tunnel”
 Goals
Securely extend
internal network
Protect data during
transmission
Maintain security of
system
 Two categories
Remote-Access VPNs
Site-to-Site VPNs
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Copyright © 2015 M. E. Kabay. All rights reserved.
VPN Technology Concepts
 See other chapters in CSH6 for background concepts,
terminology, details & readings
Chapter 5: Data Communications & Information
Security
Chapter 6: Network Topologies, Protocols & Design
Chapter 7: Encryption
Chapter 26:
Gateway Security
Devices
Chapter 37: PKI &
Certificate
Authorities
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Copyright © 2015 M. E. Kabay. All rights reserved.
Remote-Access VPNs
IPSec
Transport-Layer Security
User-Authentication Methods
Infrastructure Requirements
Network-Access
Requirements
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Copyright © 2015 M. E. Kabay. All rights reserved.
IPSec
 Basics
Suite of Internet Protocol (IP) layer
protocols
Establish & protect VPN transmissions
Usually uses client-resident application
Create encrypted VNP tunnel into internal
network
 Topics
Key Exchange & Management
Authentication Header vs Encapsulating
Security Payload
Transport vs Tunnel Mode
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Copyright © 2015 M. E. Kabay. All rights reserved.
IPSec: Key Exchange &
Management
 Must establish and manage Security Association (SA)
between client & server
 IPSec uses Internet Key Exchange (IKE)
Good reference: NIST Guide to IPSEC
VPNs (SP 800-77)
 2 phases in establishing SA
Phase 1 creates initial
IKE SA
Can use 2 modes:
 Main mode
 Aggressive mode
Phase 2 establishes IPSec SA
More details on
following slides
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IKE Phase 1 Main Mode
 Most commonly used
 3 pairs of packets
1st pair negotiates 4-parameter protection suite
Encryption algorithm (e.g., 3DES, AES)
Integrity protection algorithm (e.g., HMAC-SHA-1)
Authentication method (e.g.,
shared key, PKI certificate)
Diffie-Hellman group* (category of keylength &
type of encryption algorithm)
2nd pair exchanges encryption keys using D-H
3rd pair authentications each side of connection to
other
*See SP800-77
pp 3-11 & 3-12
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HMAC: hashed message
authentication code
Copyright © 2015 M. E. Kabay. All rights reserved.
IKE Phase 1 Aggressive Mode
 3 packets (not pairs of packets)
1st & 2nd packets
Negotiate all IKE SA
parameters
Perform key exchange
2nd & 3rd packets
Authenticate end-points
to each other
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IKE Phase 2
 Quick mode to establish IPSec SAs
 Each side maintains IPSec SA in SAD (Security Association
Database)
 Initiating device creates & sends
SA proposal to VPN server
 VPN server replies with SA
selection & hash to
authenticate connection
 Initiating device replies
with hash generated
from prompt received
from server
 If server matches received
hash with sent hash, server
adds SA to SAD &
connection proceeds
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IPSec: AH vs ESP
 Authentication Header (AH)
Protects integrity of packet
header & payload
Uses cryptographic hashing
 Encapsulating Security
Payload (ESP)
More common
implementation today
Encrypt entire packet
Create new IP header
Protects both integrity &
confidentiality
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IPSec: Transport vs Tunnel Mode
 Transport mode
Preserves original IP header
Provides confidentiality &
integrity protection for payload
Incompatible with Network
Address Translation (NAT)
TCP integrity checks fail
NAT alters IP address during
transmission – therefore
IPSec hash will be incorrect
 Tunnel mode
Protects both header and payload
Primary method today for host-to-gateway &
gateway-to-gateway VPNs
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Transport-Layer Security
(TLS)
 TLS provides protection of client/server links
 Most common implementation: SSL (Secure
Sockets Layer) → HTTPS
 Basics
128-bit encryption
Widely available on browsers & servers
Client* provides SSL-related parameters
for establishing HTTPS connection to
server
Server responds with its SSL parameters +
digital certificate
Client authenticates server
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User-Authentication
Methods
 Simplest method: user name & password
 Other methods
RADIUS: Remote Authentication Dial-In User
Service
LDAP: Lightweight Directory Access Protocol
Kerberos: access control system
Developed at MIT in 1980s
Accepted by IETF in 2003
See http://www.ietf.org/rfc/rfc1510.txt
Diagram from CDE on next slide
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Kerberos
 Login: user PW
encrypted & sent to
KDC
 KDC
Authenticates PW
Sends master
ticket (a kind of
session key) to
user
 User sends master
ticket to KDC when
requesting service
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Copyright © 2015 M. E. Kabay.
Used by kind permission of the author.
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http://www.computerlanguage.com
All rights reserved.
Infrastructure Requirements
 VPN should be outside firewall
 Connection to internal networks protected by
firewall
Restrict all external connections to internal
network
Allow encrypted connections to VPN
server to be relayed through firewall
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Network-Access
Requirements
 IPSec
Can use split tunneling for better throughput
Enforce encryption on inbound traffic
Allow outbound traffic to Internet to be treated
normally (not through encrypted tunnel)
But lose ability to inspect outbound traffic
 TLS/SSL
Dashboard allows administrator to control
settings
Current implementations similar to IPSec
flexibility
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Site-to-Site VPNs
 VPNs mostly used for client remote access
 But also used for secure internal
communications
Can create equivalent of secure WAN
(Wide Area Network)
Reduce complexity of physically-wired
WAN
 Topics in next slides relating to Trusted VPNs
MPLS
Site-to-Site VPNs
Information Assurance Considerations
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MPLS: Multiprotocol Layer
Switching (1)
 Not traditional encrypted VPN
 Similar service
 Complex issues in
deployment
 Service providers differ
in offerings
 Topics on next slides:
Purpose
Requirements
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MPLS (2): Purpose
 Typical WAN topologies = star, ring or mesh (or
combinations)
 MPLS creates
 Meshed
 Routed
 Virtual network at
 Service provider level
 MPLS free to route packets from 1 WAN endpoint to
another in virtual network
 Eliminates hub as single point of failure
 Can provide multiple QoS (quality of service) levels
 Prioritize traffic
 Allow specific protocols more bandwidth at times
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Site-to-Site (S2S) VPNs
 Purpose
 Extend WAN concepts to areas where traditional direct
connections (T1, frame relay…) are too expensive
 Leased lines be too slow
 Alternative WAN
 Use / share Internet connection
 Higher bandwidth, lower cost
 Backup
 Redundancy at relatively
low cost
 Requirements
 Internet, VPN end-points (routers)
 Possibly VPN-enabled gateway security device (firewall)
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Copyright © 2015 M. E. Kabay. All rights reserved.
IA Considerations
 Remote-access VPN Considerations
 Fidelity of Mobile Device
 VPN Client Management
 Protection of VPN Device
 Cryptographic Options
 Traffic Inspection
 Processing Power
 Interception
 Site-to-Site VPN Considerations
 Implications of Elusive VPNs
 Impact of IPv6
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Copyright © 2015 M. E. Kabay. All rights reserved.
IA Considerations
 Remote-access VPN Considerations
By nature of VPN, assuming
hostile environment for data
transmission
 Fidelity of Mobile Device
Essential to protect laptops,
phones…
Firewall, antivirus, patches, encryption
Status may change during connection
Network Access Control (NAC)
Interrogate connecting device at login
Verify security status
Complex management issue
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VPN Client Management
 IPSec requires client-side app or embedded OS
 Need to maintain up-to-date configuration
 Avoid user involvement
Push updates rather than
pulling
 TLS/SSL VPN less complex to
administer
Automatic downloads of
small Java applets or ActiveX
controls
Code can remain resident –
avoid delay at re-initiation of
sessions
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Copyright © 2015 M. E. Kabay. All rights reserved.
Protection of VPN Device
 Configure firewall to stop access to all unused ports
 Remove unacceptable cryptographic modes
 Limit access to network management protocols
such as ICMP & SNMP using ACLs
 Don’t allow insecure protocols such as FTP or HTTP
for administration
 Use strong I&A
(e.g., token-based,
two-factor)
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Copyright © 2015 M. E. Kabay. All rights reserved.
Cryptographic Options
 Selection of cryptographic protocol
During IKE negotiation
 Cipher suite determines what is available
Remove unacceptably weak protocols from
cipher suite
Prevents incompatible clients from
connecting
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Traffic Inspection
 Encrypted traffic on VPN interferes with content
inspection
 Limit inspection to post-decryption packets
inside network after VPN device
processes data stream
 Some VPN systems do
provide administrative
dynamic decryption of
packets for content
inspection
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Processing Power
 VPN can easily become a bottleneck
 Monitor processing power required to maintain
bandwidth
 Increase dedicated VPN
devices as number of
connections increases
 Can sometimes add
hardware
encryption
accelerators
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Interception (1)
 Possible to capture packets
Datagram Protocol spreads packets over
multiple routes
Thus end-point interception only practical
approach
Massively parallel computational power
can crack encryption
 Man-in-the-middle (MITM) attack
While VPN session being established
Address Resolution Protocol (ARP)
poisoning to redirect traffic to attacker’s
system
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Interception (2)
 IPsec MITM vector: preshared key
Group name & password
Authenticate IPsec connection
Fiked emulates VPN termination & collects user
credentials
Can defend using client or computer certificate for IPsec
authentication
 SSLStrip (2009)
ARP-poisoning to intercept client request for TLS/SSL
Establishes valid TLS/SSL session with server
Creates HTTP session with user but puts fake lock icon
into browser window
Can reduce risk by forcing use of direct TLS/SSL
connections, not redirection from HTTP to HTTPS
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Copyright © 2015 M. E. Kabay. All rights reserved.
Site-to-Site VPN Connections
Infrastructure Design
Cost
Availability
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Site-to-Site VPNs:
Infrastructure Design
 Multiprotocol Layer Switching (MPLS) changes
WAN administration
Can provide any-to-any connectivity
More difficult to troubleshoot than hub/spoke
topology
 Increased number of security devices
 Maintain Border Gateway Protocol (BGP) routing
security
Both sides must authenticate before being
added to routing table
 VPN naturally puts Internet in contact with
internal networks
Implement gateway security devices (GSD)
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Copyright © 2015 M. E. Kabay. All rights reserved.
Site-to-Site VPNs: Cost
 New / converted circuits
 QoS (quality of service)
monitoring
 Support for MPLS and routing
 Time for redesigning network
routing infrastructure
 Site-to-site (S2S) VPNs require
high processing power
May need code upgrades ($$)
 Higher administrative costs for
managing increased number of
devices
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Copyright © 2015 M. E. Kabay. All rights reserved.
Site-to-Site VPNs: Availability
 VPNs quickly become necessity
 Mobile workforce may be severely impaired if VPNs go
down
 Can load-balance across redundant systems
 Ideally, connections in process will not be dropped
 Must have redundant (independent) infrastructure elements
Internet links
Power
Other network
components
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Copyright © 2015 M. E. Kabay. All rights reserved.
Implications of Elusive VPNs
 More VPNs in use than administrators may
be aware of
GotoMyPc
Malicious VPNs such as botnet control
channels
Laplink™ software could allow
unauthorized access to work PC
 Bypass normal administrative controls
 Peer-to-peer (P2P) networks use VPN-like
features
 Skype can encrypt voice calls and file
transfers
 Must plan for these in defining policies
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Copyright © 2015 M. E. Kabay. All rights reserved.
Impact of IPv6
 We are running out of IPv4 address space (or
have already)
 Yet migration to IPv6 still not evident in real
world
 Verify that VPN infrastructure is IPv6
compliant
 Expect to have to translate IPv6 into IPv4 for
foreseeable future
 IPv6 does provide support for IPSec
automatically
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Copyright © 2015 M. E. Kabay. All rights reserved.
Extranets
Information
Assurance Goals
Extranet Concepts
Types of Extranet
Access
Information
Assurance
Considerations
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Copyright © 2015 M. E. Kabay. All rights reserved.
Extranets: Information
Assurance Goals
 Protecting shared information
assets
Increased security issues with
external accessors
Competitive advantage,
regulatory requirements
 Preventing information exposure
Principle of least privilege
Identity management
Access management
 Minimizing ancillary risks
Restrict outsiders’ access to
non-essential services
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Copyright © 2015 M. E. Kabay. All rights reserved.
Extranet Concepts
 Service NW vs DMZ
Don’t count on DMZ (weak security) for extranet
services
Define specific firewall architecture with particular
settings for extranet servers
 N-Tier Architecture
Distribute functions across multiple servers
E.g., separate front-end user-server from back-end
database server
 SSL Encryption
Enforce HTTPS Secure Sockets Layer traffic
Verify that padlock icon is implemented correctly
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Copyright © 2015 M. E. Kabay. All rights reserved.
Types of Extranet Access
 Vendor/Partner Information Sharing
 ERP (enterprise resource planning)
 SCM (supply chain management)
 E-Commerce
 EDI (electronic data interchange)
 CRM (customer relationship
management)
 B2B (business to business)
 B2C (business to client)
 Employee Self-Service
 E-mail
 Benefits systems
 Access to intranet systems
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Norwich University extranets
* owa for e-mail
* my.norwich.edu
* BannerWeb
Extranets: Information
Assurance Considerations (1)
 Technical Security
Cannot secure using only
a single point
Need security at multiple
layers
 Traffic Inspection
Difficult between nodes
May have to inspect traffic on extranet server before
encryption
Increases processing load on server CPU
Or may terminate SSL upstream and send cleartext data
to extranet server
Relieves extranet server of need for decryption /
encryption processing
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Copyright © 2015 M. E. Kabay. All rights reserved.
Extranet IA Considerations (2)
 Internal Network Exposure
Compromise of extranet
server must not allow
breach of inside
resources
Ensure appropriate
firewalls to shield
internal networks from
extranet
 Server
Harden servers by removing vulnerable unused services
Configure for minimum functionality required
Close attention to patches
Intrusion prevention/detection devices
Virtualization has additional complexities
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Copyright © 2015 M. E. Kabay. All rights reserved.
Extranet IA Considerations (3)
 Application
Many systems susceptible to common attacks
Buffer overflows
BO: failure to prevent data
outside bounds of a buffer
SQL injection
Cross-site scripting (XSS) from being accepted in
input and then used.
Developers must keep
security in mind throughout
SQLI: DB query sw
process
doesn’t test query
statement for correctness.
Use best practices
Stay current on threat
XSS: Browser executes
landscape
hostile script; e.g., hiding
code in bogus URL for
non-existent page.
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Copyright © 2015 M. E. Kabay. All rights reserved.
Extranet IA Considerations (4)
 Policies
Provide written policies about requirements for access &
use
Establish expectations
Useful for legal
proceedings
 Access & Identity
Management
I&A support access
controls
But passwords a poor
authentication method
Better: issuing digital certificates
 Availability: critical issue – plan for it!
 Impact of IPv6: infrastructure support issues
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Copyright © 2015 M. E. Kabay. All rights reserved.
Now go and
study
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